Cuba Libre Meets Duxbury Bay

Sign up for our weekly home and property newsletter, featuring homes for sale, neighborhood happenings, and more.

Photograph by Brian Finke

When you spend most of your professional time throwing magnificent parties for Boston’s elite, sometimes you just want to throw one for yourself. Which is precisely how locally renowned event planner and philanthropist Lynn Dale, of Lynn Dale Events, ended up holding a midsummer soiree at her waterfront Duxbury home.

“I said, ‘Let’s have a small cocktail party on the water,’ but I wanted something carefree, a little silly, and unexpected,” Dale says. As a board member, she’s helped put on philanthropic galas for local organizations ranging from the Emerald Necklace Conservancy to the Boston Lyric Opera. But for her own celebration, she wanted to take things in a different direction: “I was thinking to not do the traditional thing, where you have people show up on a summer night and you feed them stuff with mayonnaise. You know, the usual.”

What she created on the sprawling bayside lawn of her 1812 home was anything but the usual. Her chosen theme? Cuba.

Clockwise from top left: Bright espadrilles kick off the colorful celebration; Lynn Dale and her husband, Frank Wisneski; Karen Weiss indulges in a cigar; vibrant and spicy hors d’oeuvres are passed about; caterer extraordinaire Holly Safford chats with guests including Walter Whalen and Kelley Doyle; Frank Wisneski, dapper in a white dinner jacket, mingles with Michael Stansky to his right and Brackett Denniston to his left; delights include “cigars” of pulled pork on crushed “ash” made of black-and-white sesame seeds; a trumpet player keeps everyone on the dance floor. Center: Broadcast journalist Bianca de la Garza and Elisha Daniels. / Photographs by Brian Finke

Guests arrived at the historical Federal-style brick home on Powder Point Avenue (one of the South Shore’s most exclusive neighborhoods) to find its flower-filled lawn bustling with a mix of more than 100 attendees, all of whom had clearly embraced the Havana-inspired dress code. And the evening that ensued proved to be an exuberant, downright magical ode to the spirit of the newly accessible island—complete with salsa and mambo dancing, professional cigar rollers, and cheeky oversize pink blow-up flamingos bobbing in Dale’s pool.

“Even for people who go to a lot of parties all the time, Lynn’s parties are memorable and spectacular,” declared personal stylist Elisha Daniels, her watermelon mojito glowing against her Alice + Olivia top and electric-orange Chanel clutch. “She just never misses a beat. It’s always the best of the best. Best food, great décor and themes and locations, and then she puts together a group of really awesome people.” As if on cue, a platter of warm traditional Cubano sandwiches and twice-baked plantains floated by, earning a smile of approval from local broadcast journalist Bianca de la Garza. “Isn’t this all so great?” she exclaimed.

The evening’s wildly creative food came courtesy of the Catered Affair (TCA), whose tasty offerings have been gracing Boston’s top-tier parties since 1979. TCA founder and longtime Duxbury resident Holly Safford attended the party, as did her son (and TCA vice president) Andrew Marconi, who worked closely with Lynn to brainstorm this authentic yet imaginative menu. One of the evening’s biggest showstoppers: passed platters of edible “cigars”—pulled pork rolled in collard greens, then fastened with an edible wrapper. To complete the culinary trompe l’oeil, each one sat on top of convincing-looking “ashes” of crushed black-and-white sesame seeds.

Pops of pink spice up the party, as do fruity cocktails. / Photograph by Brian Finke

Equally delicious and buzzed-about throughout the night was everything that came from the ceviche bar, set by the pool in a yard dramatically drenched in purple-and-green lighting that flickered on the pines towering above. Bamboo cups of scallop with mango were a favorite of guests making their way to and from the dance floor within the glowing tent, where they swayed to the salsa tunes of a live band featuring a trumpet player who used to play with Buena Vista Social Club.

“I’m so glad Lynn and Frank decided to go this way,” Marconi observed. “This was unlike anything else Duxbury has ever seen before.” Other guests agreed: “It takes a girl with a lot of sass to pull off something like this,” said Daniels, who was one of the last revelers to leave the dance floor.

After all the cigars had been smoked (“I found labels hither and yon all over the lawn the next morning,” Dale said, with a laugh) and the Cuba Libre cocktails imbibed, it was time to leave this tropical oasis behind and return to reality. But not before one parting gift: Between goodbye hugs, guests lined up for a nightcap of boozy Cuban coffee, served with dulce de leche ice cream and rum—a final touch as sweet and surprising as the night itself.

Bianca de la Garza with Skip Patton; guests kick off their shoes and frolic on the lawn; mojitos are especially refreshing when served in Mason jars; partygoers dance until the wee hours. / Photographs by Brian Finke